2-Phenoxy and 2-phenylthio anthraquinone disperse dyes

ABSTRACT

The present invention relates to 2-phenoxy or 2-phenylthio anthraquinone compounds which bear a group of formula VI, ##STR1## bound to the para position of the phenoxy or phenylthio group, IN WHICH R 3  is hydrogen; (C 1-6 )alkyl; (C 1-3 )alkyl monosubstituted by hydroxyl, cyano, (C 1-2 )alkylcarbonyloxy, (C 1-2 )alkoxycarbonyl or (C 1-2 )alkoxycarbonyloxy; (C 2-6 )alkenyl; phenyl; or tolyl; 
     R 4  is --(CH 2 ) n  -- or --CH(R 10 )--, 
     R 5  is (C 2-6 )alkylene;--R 11  --O--R 12  -- or --CH 2  CH 2  --0--CH 2  CH 2  --O--CH 2  CH 2  --, 
     R 6a  is (C 1-12 )alkyl; (C 1-12 )alkyl monosubstituted by chlorine, bromine or hydroxyl; unsubstituted phenyl(C 1-2 )-alkyl, (C 5-7 )cycloalkyl or phenyl; or phenyl or phenyl(C 1-2 )alkyl in which the phenyl ring is monosubstituted by chlorine, bromine or methyl, 
     R 10  is (C 1-6 )alkyl or phenyl, 
     Each of R 11  and R 12 , independently, is (C 2-6 ) alkylene, 
     M is 0 or 1, and 
     N is 1, 2, 3, 4 or 5, which compounds are useful as disperse dyestuffs for dyeing or printing substrates dyeable with disperse dyes, especially linear aromatic polyester and cellulose triacetate.

IMPROVEMENTS IN OR RELATING TO ORGANIC COMPOUNDS

The present invention relates to anthraquinone compounds.

The present invention provides 2-phenoxy or 2-phenylthio anthraquinone disperse dyestuffs which bear a group of formula VI, ##STR2## bound to the para position of the phenoxy or phenylthio group, IN WHICH R₃ is hydrogen; (C₁₋₆)alkyl; (C₁₋₃)alkyl monosubstituted by hydroxyl, cyano, (C₁₋₂)alkylcarbonyloxy, (C₁₋₂) alkoxycarbonyl or (C₁₋₂)alkoxycarbonyloxy; (C₂₋₆)alkenyl; phenyl; or tolyl;

R₄ is --(CH₂)_(n) -- or --CH(R₁₀)--,

R₅ is (C₂₋₆)alkylene; --R₁₁ --O--R₁₂ -- or --CH₂ CH₂ --O--CH₂ CH₂ --O--CH₂ --,

R_(6a) is (C₁₋₁₂)alkyl; (C₁₋₁₂)alkyl monosubstituted by chlorine, bromine or hydroxyl; unsubstituted phenyl(C₁₋₂)-alkyl, (C₅₋₇) cycloalkyl or phenyl; or phenyl or phenyl(C₁₋₂) alkyl in which the phenyl ring is monosubstituted by chlorine, bromine or methyl,

R₁₀ is (C₁₋₆)alkyl or phenyl,

Each of R₁₁ and R₁₂, independently, is (C₂₋₆) alkylene,

M is 0 or 1, and

N is 1, 2, 3, 4 or 5.

It will be appreciated that the anthraquinone nucleus must bear at least one chromophoric substituent in the 1-, 4-, 5- or 8-position.

It will also be appreciated that the anthraquinone nucleus and the benzene nucleus of the 2-phenoxy or 2-phenylthio group may bear further substituents which are common in the chemistry of anthraquinone disperse dyestuffs. However, substituents or combinations thereof which are known deleteriously to affect the dyeing properties of the molecule, as well as substituents or combinations which are known to give rise to steric and/or stability problems should not, of course, be present in the molecule.

As examples of substituents which give rise to stability problems may be given those which contain the groups ##STR3##

Preferably, where the benzene nucleus of the 2-phenoxy or 2-phenylthio group is substituted it is substituted by up to two chlorine or bromine atoms or monosubstituted by methyl or (C₁₋₂)alkoxy.

The preferred chromophoric substituents include hydroxy and --NHR₉ in which R₉ is hydrogen, (C₁₋₆)alkyl, (C₅₋₇)cycloalkyl or phenyl. The molecule preferably contains two chromophoric substituents, which substituents are in the 1- and 4-positions. Any further substituents on the anthraquinone nucleus are preferably chlorine or bromine atoms. Preferably the anthraquinone nucleus is further unsubstituted or is further substituted by a single chlorine or bromine atom, especially in the 3-position.

Preferred compounds of the invention are those of formula I', ##STR4## in which R₁ is --O-- or --S--, R₃ to R₅ and m are as defined above,

R₆ is (C₁₋₁₂)alkyl; (C₁₋₆) alkyl monosubstituted by chlorine, bromine or hydroxyl; unsubstituted phenyl (C₁₋₂)alkyl, (C₅₋₇)cycloalkyl or phenyl; or phenyl(C₁₋₂)alkyl or phenyl in which the phenyl ring is monosubstituted by chlorine, bromine or methyl,

R₇ is hydrogen, chlorine or bromine,

R₈ is hydroxyl or --NHR₉,

R₉ is as defined above,

either, R₁₃ and R₁₄ are both hydrogen, chlorine or bromine,

or one of R₁₃ and R₁₄ is hydrogen and the other is methyl or (C₁₋₂)alkoxy.

Any unsubstituted alkyl as R₃ is preferably straight chain and contains 1 to 4 carbon atoms.

Any alkyl as R₁₀ is preferably straight chain and contains 1 to 3 carbon atoms.

Any alkylene as R₅ may be branched or straight chain and preferably is a (C₂₋₄)alkylene. More preferably any alkylene as R₅ is a (C₂₋₃)alkylene.

Any unsubstituted alkyl as R_(6a) or R₆ may be straight chain or branched and preferably contains 1 to 6 carbon atoms. Any substituted alkyl as R_(6a) or R₆ is preferably straight chain and contains up to 4 carbon atoms and is substituted in the β-, δ- or δ-position, preferably in the ω-position. Where R_(6a) or R₆ is phenyl, preferably the phenyl is unsubstituted or substituted by chlorine or methyl. Any phenylalkyl as R_(6a) or R₆ is preferably unsubstituted or substituted by methyl or chlorine. Any cycloalkyl as R_(6a) or R₆ is preferably a C₅ or C₆ cycloalkyl.

Any alkyl as R₉ may be straight chain or branched and preferably contains 1 to 4 carbon atoms. Any cycloalkyl as R₉ is preferably cyclohexyl. Preferably the group --NHR₉ is --NH₂, (C₁₋₄)alkylamino, cyclohexylamino or phenylamino.

Preferably R₁ is --O--.

R₃ is preferably R₃ ', where R₃ ' is hydrogen or (C₁₋₄)alkyl. More preferably R₃ is R₃ ", where R₃ " is hydrogen or methyl.

R₄ is preferably R₄ ', where R₄ ' is --(CH₂)_(n), where n' is 1, 2, 3 or 5, preferably 1, 2 or 5, especially 1, or --CH(R₁₀ ')--, where R₁₀ ' is a linear (C₁₋₃)alkyl or phenyl.

R₅ is preferably R₅ ', where R₅ ' is (C₂₋₄) alkylene or --CH₂ CH₂ --O--CH₂ CH₂ --. More preferably R₅ is R₅ ", where R₅ " is 1,2-ethylene, 1-methyl-1,2-ethylene or --CH₂ CH₂ --O--CH₂ CH₂ --, especially 1,2-ethylene.

R₆ is preferably R₆ ', where R₆ ' is (C₁₋₆)alkyl, β-, γ- or δ-hydroxy(C₂₋₄)alkyl, especially ω-hydroxy(C₂₋₄)alkyl, (C₅₋₆)cycloalkyl, β-chloro- or bromoethyl, phenyl, chlorophenyl, tolyl, chlorobenzyl, phenyl(C₁₋₂)alkyl or tolylethyl, especially (C₁₋₆)alkyl.

R₇ is preferably hydrogen.

R₈ is preferably R₈ ', where R₈ ' is hydroxyl, --NH₂, (C₁₋₄)alkylamino, cyclohexylamino or phenylamino, more preferably hydroxyl.

R₁₃ and R₁₄ are preferably R₁₃ ' and R₁₄ ', where either R₁₃ ' and R₁₄ ' are both hydrogen or chlorine, or one of R₁₃ ' and R₁₄ ' is hydrogen and the other is methyl or (C₁₋₂) alkoxy. More preferably, R₁₃ and R₁₄ are both hydrogen.

m is preferably O.

Preferred compounds of formula I' are those in which R₃ is R₃ ', R₄ is R₄ ', R₅ is R₅ ', R₆ is R₆ ', R₇ is hydrogen, R₈ is R₈ ' and R₁₃ and R₁₄ are R₁₃ ' and R₁₄ ', with those compounds where R₁ is oxygen and where R₁₃ and R₁₄ are both hydrogen and m is O being even more preferred.

Especially preferred compounds of formula I' are those in which R₁ is oxygen, R₃ is R₃ ', R₄ is R₄ ', R₅ is R₅ ', preferably R₅ ", R₆ is R₆ ', R₇ is hydrogen, R₈ is R₈ ' and R₁₃ and R₁₄ are both hydrogen, with those compounds where R₅ is 1,2-ethylene, R₆ is (C₁₋₆)alkyl, R₃ is R₃ ", n is 1,2 or 5, especially 1, m is O and R₈ is hydroxyl being most preferred.

The present invention also provides a process for the production of the 2-phenoxy or 2-phenylthio anthraquinone compounds of the invention comprising

(a) condensing a corresponding 2-parasulphophenoxy or 2-parasulphophenylthio anthraquinone, or a functional derivative thereof, with a compound of formula II,

    r.sub.3 --nh--r.sub.4 --co--o--(r.sub.5 o).sub.m --R.sub.6 II

or

(b) esterifying a corresponding 2-phenoxy or 2-phenylthio anthraquinone having a group of formula III

    --so.sub.2 --nr.sub.3 r.sub.4 cooh                         iii

or a functional derivative thereof,

in the para position of the 2-phenoxy or 2-phenylthio benzene nucleus,

with an alcohol of formula IV,

    ho--(r.sub.5 --o).sub.m --R.sub.6                          IV

the above reactions may be carried out in accordance with known methods. Preferred functional derivatives of the sulphonic acid and carboxylic acid are the acid halides, in particular the acid chloride.

The starting materials for the above processes are either known or may be obtained in conventional manner from available starting materials.

The resulting compounds of the invention may be isolated in conventional manner.

The dyestuffs according to the invention are useful as disperse dyes for dyeing or printing substrates dyeable with disperse dyes, e.g. consisting of or comprising synthetic or semi-synthetic, hydrophobic, high molecular weight organic materials. Preferred substrates are those which consist of linear aromatic polyester or cellulose triacetate. The substrate is preferably textile and may, for example, be in loose fibre, fabric or yarn from. Dyeing or printing may be carried out in accordance with known methods, for example, as described in French Patent No. 1,445,371.

The dyestuffs may be made up into dyeing preparations in accordance with known methods, for example by grinding in the presence of dispersing agents and/or fillers, with subsequent spray or vacuum drying.

The dyeings obtained possess notable light and thermofixation fastness. They are also notably fast to permanent pleating, washing and sweat. The dyes build-up well, especially on polyester. They give even dyeings on stripy polyester.

The following Examples further serve to illustrate the invention. In the Examples the parts are by weight and the temperatures are in degrees Centigrade.

EXAMPLE 1

(a) 12 Parts of 1-amino-2-(4'-chlorosulphonyl-phenoxy)-4-hydroxyl anthraquinone, 5 parts of glycinebutylester hydrochloride and 3 parts of triethylamine in 60 parts of dimethylformamide are heated to 60°. At this temperature a solution of 3 parts of triethylamine in 10 parts of diethylformamide is added dropwise over a period of 30 minutes. The reaction mixture is held for a further 30 minutes at 60° and is then poured into 600 parts of water. The product of formula ##STR5## is filtered, washed with water until the filtrate is colourless and dried in vacuo.

(b) 12 Parts 1-amino-2-(4'-carboxymethylsulphamyl-phenoxy)-4-hydroxyanthraquinone are added to a solution of 3 parts of hydrochloric acid in 600 parts n-butanol and are heated to the boil. Water produced during the reaction is removed by azoetropic distillation. After completion of the reaction the mixture is concentrated and poured onto water. The product which is identical to that obtained above under procedure (a) is filtered, washed with water and dried in vacuum.

In the following Table 1, further dyestuffs of formula I' are given which may be prepared in analogy with the procedures of Example 1. In all cases R₁ is oxygen, R₇ is hydrogen, R₈ is --OH and R₁₃ and R₁₄ are hydrogen. The dyestuffs dye polyester fibre in red shades.

                                      TABLE 1                                      __________________________________________________________________________     Example                                                                        No.  R.sub.3                                                                            R.sub.4                                                                               m R.sub.5         R.sub.6                                      __________________________________________________________________________     2    H   CH.sub.2                                                                              0 --              CH.sub.3                                     3    "   "      0 --              C.sub.2 H.sub.5                              4    "   "      0 --              (CH.sub.2).sub.2 CH.sub.3                    5    "   "      0 --              CH(CH.sub.3).sub.2                           6    "   "      0 --              CH.sub.2CH(CH.sub.3).sub.2                   7    "   "      0 --                                                                                              ##STR6##                                    8    "   "      0 --              (CH.sub.2).sub.4 CH.sub.3                    9    "   "      0 --                                                                                              ##STR7##                                    10   "   "      0 --              (CH.sub.2).sub.5CH.sub.3                     11   "   "      0 --                                                                                              ##STR8##                                    12   "    CH.sub.2 CH.sub.2                                                                    0 --                                                                                              ##STR9##                                    13   "   "      0 --                                                                                              ##STR10##                                   14   "   CH.sub.2                                                                              0 --              CH.sub.2C.sub.6 H.sub.5                      15   "   "      0 --                                                                                              ##STR11##                                   16   "   "      1 CH.sub.2 CH.sub.2                                                                              CH.sub.3                                     17   "   "      1 "               C.sub.2 H.sub.5                              18   "   "      1 "               CH(CH.sub.3).sub.2                           19   "   "      1 "               (CH.sub.2).sub.3 CH.sub.3                    20   "   "      1 "               C.sub.6 H.sub.5                              21   "   "      1                                                                                 ##STR12##      CH.sub.3                                     22   "   "      1 CH.sub.2 CH.sub.2OCH.sub.2CH.sub.2                                                             "                                            23   "   "      1 "               C.sub.2 H.sub.5                              24   "   "      1 "               (CH.sub.2).sub.3 CH.sub.3                    25   CH.sub.3                                                                           "      0 --              C.sub.2 H.sub.5                              26   "   "      0 --              (CH.sub.2).sub.3 CH.sub.3                    27   H                                                                                   ##STR13##                                                                            0 --              "                                            28   "   "      1 CH.sub.2 CH.sub.2                                                                              C.sub.2 H.sub.5                              29   "                                                                                   ##STR14##                                                                            0 --              "                                            30   "                                                                                   ##STR15##                                                                            0 --              CH.sub.3                                     31   "   CH.sub.2 CH.sub.2                                                                     0 --              C.sub.2 H.sub.5                              32   "   "      0 --              (CH.sub.2).sub.2 CH.sub.3                    33   "   "      0 --              CH(CH.sub.3).sub.2                           34   "   "      0 --              (CH.sub.2).sub.3 CH.sub.3                    35   "   "      0 --              CH.sub.3                                     36   "   "      0 --                                                                                              ##STR16##                                   37   "   "      0 --              (CH.sub.2).sub.4 CH.sub.3                    38   "   "      0 --              (CH.sub.2).sub.5 CH.sub.3                    39   "   "      1 CH.sub.2 CH.sub.2                                                                              CH.sub.3                                     40   "   "      1 "               C.sub.2 H.sub.5                              41   "   "      1 "               CH(CH.sub.3).sub.2                           42   "   "      1 CH.sub.2 CH.sub.2OCH.sub.2 CH.sub.2                                                            CH.sub.3                                     43   "   (CH.sub.2).sub.3                                                                      0 --              "                                            44   "   "      0 --              C.sub.2 H.sub.5                              45   "   "      0 --              CH(CH.sub.3).sub.2                           46   "   "      0 --              (CH.sub.2).sub.3 CH.sub.3                    47   "   "      1 CH.sub.2 CH.sub.2                                                                              CH.sub.3                                     48   "   (CH.sub.2).sub.5                                                                      0 --              "                                            49   "   "      0 --              C.sub.2 H.sub.5                              50   "   "      0 --              CH(CH.sub.3).sub.2                           51   "    CH.sub.2                                                                             0 --              CH.sub.2 CH.sub.2Cl                          52   "   "      0 --              CH.sub.2 CH.sub.2Br                          53   "   "      0 --              (CH.sub.2).sub.4OH                           54   "   "      1 CH.sub.2 CH.sub.2                                                                               ##STR17##                                   55   "   "      1 "                                                                                               ##STR18##                                   56   "   "      0 --                                                                                              ##STR19##                                   57   "   "      0 --                                                                                              ##STR20##                                   58   "   "      0 --                                                                                              ##STR21##                                   59   "   "      0 --                                                                                              ##STR22##                                   60   CH.sub.3                                                                           "      0 --              CH.sub.3                                     61   "   "      0 --              CH(CH.sub.3).sub.2                           62   "   "      0 --              CH(CH.sub.3)C.sub.2 H.sub.5                  63   "   "      0 --              CH.sub.2 CH(CH.sub.3).sub.2                  64   H                                                                                   ##STR23##                                                                            0 --              CH.sub.3                                     65   "   "      0 --              C.sub.2 H.sub.5                              66   "   "      0 --              CH(CH.sub.3).sub.2                           67   "   "      0 --              CH(CH.sub.3)C.sub.2 H.sub.5                  68   "   "      0 --              CH.sub.2 CH(CH.sub.3).sub.2                  69   "   "      1 --              CH.sub.3                                     __________________________________________________________________________

further dyestuffs of formula ##STR24## which are prepared in analogous manner to the procedure described in Example 1, are given in Table 2. The dye shade on polyester fibre is given in each case.

                                      TABLE 2                                      __________________________________________________________________________     Example                     Shade on poly-                                     No.  R.sub.1                                                                            R      R.sub.7                                                                           R.sub.8  ester fibre                                        __________________________________________________________________________     70   S                                                                                   ##STR25##                                                                            H  OH       violet                                             71   O   "      Cl "        red                                                72   "   "      Br "        "                                                  73   "                                                                                   ##STR26##                                                            74   "                                                                                   ##STR27##                                                                            "  "        "                                                  75   "                                                                                   ##STR28##                                                                            "  "        "                                                  76   "                                                                                   ##STR29##                                                                            "  "        "                                                  77   "                                                                                   ##STR30##                                                                            "  NH.sub.2 violet                                             78   "   "      "  NHC.sub.2 H.sub.5                                                                       blue                                               79   "   "      "                                                                                  ##STR31##                                                                              "                                                  80   "   "      "                                                                                  ##STR32##                                                                              "                                                  81   S   "      "                                                                                  ##STR33##                                                                              "                                                  __________________________________________________________________________

application example a

6 parts of the dyestuff of Example 1 are ground with 14 parts of the sodium salt of lignin sulphonic acid, 180 parts of water and 400 parts of silica quartz beads until the average particle size is less than 1μ. The suspension is then filtered. 60 parts of the thus obtained dyestuff preparation are added to 4000 parts of water and the thus obtained dye bath, which is buffered to pH 5, is heated to 60°. 100 parts of polyester fibre fabric are added to the bath together with 30 parts of ortho phenylphenol. The bath is heated to the boil and the fabric is dyed for 1 hour at the boil. After cooling, rinsing, soaping, rinsing again and drying a brilliant bluish-red even dyeing is obtained.

The dyestuffs of Examples 2 to 81 can be used to dye polyester fibre fabric in accordance with the above procedure. 

What is claimed is:
 1. A compound of the formula, ##STR34## in which R₁ is --O-- or --S--, R₃ is hydrogen; (C₁₋₆)alkyl; (C₁₋₃)alkyl monosubstituted by hydroxyl, cyano, (C₁₋₂)-alkylcarbonyloxy, (C₁₋₂)alkoxycarbonyl or (C₁₋₂)alkoxycarbonyloxy; (C₂₋₆)alkenyl; phenyl; or tolyl;R₄ is --(CH₂)_(n) -- or --CH(R₁₀)--, R₅ is (C₂₋₆)alkylene; --R₁₁ --O--R₁₂ --or --CH₂ CH₂ --O--CH₂ CH₂ --O--CH₂ CH₂ --, R₆ is (C₁₋₁₂)alkyl; (C₁₋₆)alkyl monosubstituted by chlorine, bromine or hydroxyl; unsubstituted phenyl (C₁₋₂)alkyl, (C₅₋₇)-cycloalkyl or phenyl; or phenyl (C₁₋₂)-alkyl or phenyl in which the phenyl ring is monosubstituted by chlorine, bromine or methyl, R₇ is hydrogen, chlorine or bromine, R₈ is hydroxyl or --NHR₉, R₉ is hydrogen, (C₁₋₆)alkyl, (C₅₋₇)cycloalkyl or phenyl, R₁₀ is (C₁₋₆)alkyl or phenyl, each of R₁₁ and R₁₂, independently, is (C₂₋₆)alkylene, either, R₁₃ and R₁₄ are both hydrogen, chlorine or bromine, or one of R₁₃ and R₁₄ is hydrogen and the other is methyl or (C₁₋₂)alkoxy, m is 0 or 1, and n is 1, 2, 3, 4 or
 5. 2. A compound according to claim 1, in which R₃ is R₃ ', where R₃ ' is hydrogen or (C₁₋₄)alkyl.
 3. A compound according to claim 2, in which R₄ is R₄ ', where R₄ ' is --(CH₂)_(n'), where n' is 1, 2, 3 or
 5. 4. A compound according to claim 3, in which R₅ is R₅ ', where R₅ ' is (C₂₋₄)alkylene or --CH₂ CH₂ --O--CH₂ CH₂ --.
 5. A compound according to claim 4, in which R₆ is R₆ ', where R₆ ' is (C₁₋₆)alkyl, β-, γ- or δ-hydroxy(C₂₋₄)alkyl, (C₅₋₆)cycloalkyl, β-chloro- or bromoethyl, phenyl, chlorophenyl, tolyl, chlorobenzyl, phenyl (C₁₋₂)alkyl or tolylethyl.
 6. A compound according to claim 5, in which R₇ is hydrogen.
 7. A compound according to claim 6, in which R₈ is R₈ ', where R₈ ' is hydroxyl, --NH₂, (C₁₋₄)alkylamino, cyclohexylamino or phenylamino.
 8. A compound according to claim 7, in which R₁₃ and R₁₄ are R₁₃ ' and R₁₄ ', where either R₁₃ ' and R₁₄ ' are both hydrogen or one of R₁₃ ' and R₁₄ ' is hydrogen and the other is methyl or (C₁₋₂)alkoxy.
 9. A compound according to claim 8, in which R₁ is oxygen.
 10. A compound according to claim 9, in which m is O.
 11. A compound according to claim 10, in which R₁₃ and R₁₄ are both hydrogen.
 12. A compound according to claim 1, in which R₁ is oxygen, R₃ is R₃ ', where R₃ ' is hydrogen or (C₁₋₄)alkyl, R₄ is R₄ ', where R₄ ' is --(CH₂)_(n'), where n' is 1, 2, 3 or 5, R₅ is 1,2-ethylene, 1-methyl-1,2-ethylene or --CH₂ CH₂ --O--CH₂ --, R₆ is R₆ ', where R₆ ' is (C₁₋₆)alkyl, β-, γ- or ω- hydroxy(C₂₋₄)alkyl, (C₅₋₆)cycloalkyl, β-chloro- or bromoethyl, phenyl, chlorophenyl, tolyl, chlorobenzyl, phenyl(C₁₋₂)alkyl or tolyethyl, R₇ is hydrogen, R₈ is R₈ ', where R₈ ', where R₈ ' is hydroxyl, --NH₂, (C₁₋₄)alkylamino, cyclohexylamino or phenylamino, m is O, and R₁₃ and R₁₄ are both hydrogen.
 13. A compound according to claim 12, in which R₄ is R₄ ', where n' is 1, 2 or
 5. 14. A compound according to claim 13, in which R₅ is 1,2-ethylene.
 15. A compound according to claim 12 in which R₆ is (C₁₋₆)alkyl.
 16. A compound according to claim 12, in which R₃ is hydrogen or methyl.
 17. A compound according to claim 13, in which n is l.
 18. A compound according to claim 1, of formula, ##STR35##
 19. A compound according to claim 1, of formula, ##STR36##
 20. A compound according to claim 1, of formula, ##STR37##
 21. A compound according to claim 1, of formula, ##STR38##
 22. A disperse dye according to claim 1 wherein the chromphoric substituent is hydroxy or --NHR₉ wherein R₉ is hydrogen, (C₁₋₆) alkyl, (C₅₋₇) cycloalkyl or phenyl. 